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Transition‐Metal‐Free Synthesis of 1,2‐diphenyl‐1 H ‐benzo[ d ] Imidazole Derivatives from N ‐phenylbenzimidamides and Cyclohexanones
Author(s) -
Lu Guoqiang,
Luo Nan,
Hu Fangpeng,
Ban Zihui,
Zhan Zhenzhen,
Huang GuoSheng
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201901161
Subject(s) - chemistry , dehydrogenation , imidazole , transition metal , iodine , aryl , catalysis , medicinal chemistry , manganese , organic chemistry , alkyl
A transition‐metal‐free strategy for the formation of 1,2‐diphenyl‐1 H ‐benzo[ d ] imidazoles from N ‐phenylbenzimidamides and cyclohexanones is introduced. This is the first report on the direct synthesis of 1,2‐diphenyl‐1 H ‐benzo[ d ] imidazoles from cyclohexanones and N ‐phenylbenzimidamides via iodine‐ promoted oxidative cyclization. Non‐aromatic cyclohexanones were smoothly dehydrogenated, and acted as an aryl source using oxygen as a green oxidant. The catalytic use of iodine makes this method quite simple, more economical and convenient. Under optimized conditions, various substituted 1,2‐diphenyl‐1 H ‐benzo[ d ] imidazoles were smoothly reacted, and the desired substituted imidazoles were generated with moderate to excellent yields.